What Not to Wear (and to Wear): Kindergarten Edition

Girl's legs with striped socks

I’ve enjoyed these twenty years of teaching –- and have heard and seen it all. I’ve seen a six-year-old girl teetering into the classroom in her mother’s high heel shoes. I’ve seen a six-year-old boy wearing his grandfather’s old coke-bottle lens glasses, claiming that the doctor JUST gave them to him because he needed them. I’ve seen the ten-year-old boy wearing his camouflage pants and army shirt to school every day. I’ve seen the five-year-old boy come to school in his grandmother’s sky blue cat-woman eyeglasses, complete with studded rhinestones on the corners, claiming the doctor made him wear them after replacing his real eyes with bionic ones.

But one of my most memorable moments happened last year. It was pajama day in kindergarten, and the children could either wear PJ’s to school or bring them in their backpacks. They took turns heading into the tiny bathroom to change, smiling and singing all the way. I noticed Janie had a tiny bundle under her arm and a huge smile on her face.

As I gathered the children on the carpet, she burst out of the bathroom and pranced across the room in her mother’s tiny black negligee and what appeared to be a gorgeous black garter belt secured around her head. My mouth dropped to the floor. I am sure I laughed out loud, thanked her for modeling for us and scooted her back into the bathroom to put BACK on the Little Mermaid nightgown she had originally been wearing. I was convinced that her mother had no idea what she had smuggled into the room, but I often think of sending her a thank you note for unknowingly participating in such a wonderful memory.

I was reminded of that story this summer in summer reading camp. I heard several children barreling into the classroom laughing and giggling one morning, and looked up to see that Frank had decided to come to school in his Spiderman pajamas. And no, it was not pajama day. I smiled ear to ear as I saw him, and he was on top of the world that whole morning.

As I shared this story with a friend of mine, she looked at me intently, and said this, “I wish that I had been that mother -- the parent who let my kid go to school wearing whatever she wanted. Instead, I was the one who insisted on perfect pigtails. I remember dropping her off at school in the morning after fighting to get her hair in those perfect pigtails, and I always said that I was sorry we had a horrible morning but at least her hair looked good.”

When I look back on the years I’ve spent with the little ones, I remember fondly the children who follow their own hearts. The ones who come to school with their Dorothy slippers, wearing their grandfather’s glasses; their mother’s shoes smuggled into school in their backpacks and their polka dot shirts and striped skirts put together nicely with floral leggings. These are the children that I remember with a smile and a chuckle.

Sure, there are some rules that should be followed when sending kids to school. First, make sure they have sneakers on gym day! Some will try to avoid this, if running and breaking a sweat is not something they enjoy. Also, make sure they have snow boots in their backpacks when snow covers the ground; teachers go outside unless there’s a tornado looming or the skies have opened up. You do NOT want to be with a group of five-year-olds who have NOT had recess. Don’t send them in their Sunday best, because they surely will be playing with Play-Doh, painting, and sitting on the carpet. And last but not least, try to convince them to leave the flip-flops at home. If I had a dollar for every scraped toe, twisted ankle and tear spilled after a flip-flop accident, I would be basking in the sun at the Bahamas right now.

But perhaps the best rule of all for parents of kindergartners is this: Try to muster up the courage to let them choose what to wear, to be who they are and to wear those Dorothy slippers to school. After all, quick as a wink, they’ll be wearing nothing but Abercrombie, and you’ll be wishing for those days of glitterized shoes and glasses with feathers. Oh, but you might want to hide the negligees.

Wait, on second thought…

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